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Synthesis and QSAR study of novel cytotoxic spiro[3H-indole-3,2 '(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3 ',5 '(1H,2 ' aH,4 ' H)-triones
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2012 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 47, 312-322 p.Article in journal (Refereed) Published
Abstract [en]

1,3-Dipolar cycloaddition reaction of 1-aryl-1H-pyrrole-2,5-diones 1a-e with non-stabilized azomethine ylides, generated in situ via decarboxylative condensation of isatins 2a-c and sarcosine (3) in refluxing ethanol, afforded 4'-aryl-5'a,6'-dihydro-1'-methyl-spiro[3H-indole-3,2'(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3',5'(1H,2'aH,4'H)-triones 4a-o in good yields. Compound 4I exhibited high anti-tumor activity against HEPG2 (liver cancer) cell line (IC50 = 12.16 mu M) compared to that of Doxorubicin (IC50= 7.36 mu M), and the other synthesized compounds revealed moderate anti-tumor properties against HCT116 (colon), MCF7 (breast) and HEPG2 (liver) human tumor cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explore the structural requirements controlling the observed anti-tumor properties. It was found that the major structural factors affecting potency of these compounds were related to their basic skeleton.

Place, publisher, year, edition, pages
2012. Vol. 47, 312-322 p.
Keyword [en]
1H-pyrrole-2, 5-diones, Azomethine ylides, Spiro[3H-indole-3, 2 '(1 ' H)-pyrrolo[3, 4-c]pyrrole], Anti-tumor, QSAR
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Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-86247DOI: 10.1016/j.ejmech.2011.10.058ISI: 000301169800034OAI: oai:DiVA.org:su-86247DiVA: diva2:586529
Available from: 2013-01-11 Created: 2013-01-11 Last updated: 2017-12-06Bibliographically approved

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Stawinski, Jacek
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